5-Chloro-2'-deoxyuridine
Basic information
- CAS
50-90-8- Standard SMILES
O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1Cl- InChIKey
NJCXGFKPQSFZIB-RRKCRQDMSA-N- Molecular formula
- C9H11ClN2O5
- Average molar mass
- 262.65 g/mol
- Monoisotopic mass
- 262.0356491
Names & identifiers
- Preferred name
- 5-Chloro-2'-deoxyuridine
- IUPAC
- 5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- English name
- 5-Chloro-2'-deoxyuridine
- Molecular formula
- C9H11ClN2O5
- Molecular weight
- 262.65
Names & synonyms
5-Chloro-2'-deoxyuridine50-90-8Chlorodeoxyuridine5-ChlorodeoxyuridineUridine, 5-chloro-2'-deoxy-2'-Deoxy-5-chlorouridine55N9ZEH8KSNSC-749426RefChem:534338623-009-7CldU5-Chloro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
Show more names
CLUDRNSC-371331, CDC5-Chlorodeoxyuridin5-CHLORODESOXYURIDINE5-chloro-2’-deoxy-uridin5-Chloro-2’-deoxyuridine
MFCD000065315-Chloro-2 -deoxyuridineCHEMBL505732AKOS027447511NSC 7494265-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione5-Chlorodeoxyuridine;CldU
Database identifiers
- CAS
50-90-8- PubChem CID
- 65510
- DTXSID
DTXSID50964486- ChEMBL
CHEMBL505732- UNII
- 55N9ZEH8KS
- EC Number
- 623-009-7
- Nikkaji
- J49.656A
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 99.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 386
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
Physical DescriptionSolid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 176 · 176-179°C
- Density
- 1.5507 · 1.5507 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly), Water (Slightly)
- form
- Solid
- pka
- 7.73 · 7.73±0.10(Predicted)
- color
- White to Off-White
- InChI
- InChI=1S/C9H11ClN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
- InChIKey
- NJCXGFKPQSFZIB-RRKCRQDMSA-N
- SMILES
- OC[C@H]1O[C@@H](N2C=C(Cl)C(=O)NC2=O)C[C@@H]1O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards Summary
Teratogenicity observed in rats administered 125-1,000 mg/kg on day 12 of gestation; [Shepard's Catalog of Teratogenic Agents] Intraperitoneal LD50 (rat) = 2,000 mg/kg; [RTECS] May cause irritation; Harmful by ingestion, inhalation, and skin absorption; Suspected carcinogen; [Sigma-Aldrich MSDS] See Uridine.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- YU7400000
- hs_code
- 29349990
- risk_code
- 20/21/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 36/37/39-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H351
Chemistry & industry
Applications
Description5-Chloro-2''-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.
UsesA halogenated uridine derivative used in pharmaceutical compositions.
Uses5-Chloro-2'-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.[Cayman Chemical]
Uses5-Chloro-2′-deoxyuridine (CldU) is used as a thymidine analog to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU).
Upstream & downstream products
Upstream raw materials
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
1 records
Compound notes
Loading…